


Five times Dean spreads his legs (and the one time he finds what he seeks)

by LikeAllLoversAndSadPeople



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Bottom Dean Winchester, Coming Untouched, First Time, M/M, Manhandling, Rimming, Sibling Incest, Sub Dean
Language: English
Status: In-Progress
Published: 2020-10-17
Updated: 2021-02-07
Packaged: 2021-03-09 02:47:54
Rating: Explicit
Warnings: Underage
Chapters: 3
Words: 8,315
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27067381
Author URL: https://archiveofourown.org/users/LikeAllLoversAndSadPeople/pseuds/LikeAllLoversAndSadPeople
Summary: Dean likes girls, he's sure of that. But sometimes he just needs to be held down and taken by someone who is bigger and stronger than him. Sometimes, he just needed a good hard fucking.When he's sixteen, he finally finds the man to give him exactly what he needs. The first of five.
Relationships: Benny Lafitte/Dean Winchester, Dean Winchester/Sam Winchester, Sonny (Supernatural: Bad Boys)/Dean Winchester
Comments: 5
Kudos: 91





	1. Dean/Sonny

**Author's Note:**

  * For [Ithanelin](https://archiveofourown.org/users/Ithanelin/gifts).



> So, I've been rewatching Supernatural again and I gotta say, the more I watch it, the gayer it becomes. And that kinda triggers the fanfic part of my brain :)
> 
> This will be a 5+1 fic where Dean bottoms for a variety of reasons, ending with the one that sticks. Pairings are found above, I'll update the tags as I go along!
> 
> Final important sidenote. While I've written this pairing as consensual and sex-positive, it should be noted that a caretaker in real life should never ever lay a finger on the people in their care, no matter their age. But fiction, and smut, and Dean being a needy slut, am I right? ;)

The first time Dean spread his legs for someone who gave a crap about him, he was sixteen and left in a boy’s home by his Dad. He’d felt abandoned and alone and knew that he was being punished for leaving behind Sammy. His Dad had always been creative in coming up with fitting punishments.

If he was being honest, though, the boy’s home wasn’t half as bad as he’d feared. That Sonny dude seemed to actually care about the boys in his care and he took his time with Dean, even after all the insults and bluster on Dean’s part.

It took a while, but Dean eventually realized that his Dad wasn’t planning on coming back for him any time soon and he relaxed a bit. Without the constant threat of a new case, he found that he could actually focus on school and get decent grades.

He even got in the wrestling team, and felt a twinge of regret at not being able to show Sammy how good he was doing. That was the real punishment, he knew, Dad keeping him away from his little brother. 

Still, he made some friends, charmed his way into guitar lessons with a cute girl, and tried not to dwell on the fact how little he missed the hunter’s life.

Sonny had quickly become a constant in his life, being there for a talk or just a comfortable silence whenever Dean felt like it. Already, he felt like he could tell the man more that he could his own father. 

He saw how Sonny was with the other boys, giving them hugs if they wanted one. Dean longed for that, but couldn’t find the courage to ask. It took him a month and a half, but he finally managed to ask for a hug from the big man. 

When Sonny swept him up in a bear hug without a second’s hesitation, Dean felt some long-held tension release at the pressure and let himself go boneless in the older man’s grip.

“You okay there, D-dawg?”

Dean crinkled his nose at the nickname, still not used to it. He held on to the hug though, not answering Sonny’s question.

The man pulled away a little, trying to make eye contact. Dean avoided it stubbornly. 

“Lemme guess. Not too many hugs in your life?”

“Just from my little brother, Sammy,” Dean mumbled, still looking at his feet.

“Tell you what. From now on, you can get as many hugs as you want. The lesson boys are taught that they can’t show affection or emotion is plain bullshit. We’re all human here, and we all need a good hug from time to time. You hearin’ me?”

“Yeah, Sonny.”

“Good. Now come here.”

Sonny pulled him in again and this time, Dean hugged back. It felt safe in those arms. He smelled tobacco and dirt, with the unmistakable scent of clean sweat after a hard day’s work. 

Before Dean could really register the tangle of emotions that bubbled up, his body decided to react for him. He could suddenly feel a treacherous erection form between their bodies. 

He jerked away, ashamed of his uncontrollable body, still hardening at the slightest indication. Sonny seemed confused for a moment, before chuckling.

“It’s okay, Dean. You shouldn’t be ashamed of a natural bodily function.”

“Easy for you to say, you don’t have to deal anymore with this stupid thing going up and down all the time.”

Sonny let out a big laugh at that.

“You’re right, son. But I had my fair share of awkward boners when I was your age.”

Dean smiled at him, feeling some of the shame creep away. He tried to surreptitiously adjust himself in his pants, but of course Sonny spotted him.

“Go take care of that in peace, I’m off to take a shower anyway.”

Dean was left alone in the living room with a throbbing hard-on and a persistent image of Sonny’s big, strong body in the shower. It took him all of thirty seconds to come silently in his cupped palm.

Dean had had little time to think much about his sexuality at this point in his life. He was pretty sure he liked girls. He definitely enjoyed looking at women in porn, and he’d had enough crushes in enough pass-through towns to confirm that girls were a pretty awesome part of life.

They made him feel big and strong, a protector. He liked that feeling, liked the way their soft curves molded against his body as they kissed him. 

But there was another feeling he liked, something he knew from his upbringing he really shouldn’t. 

He’d felt it when he got a one-armed hug from Uncle Bobby, or when Pastor Jim squeezed his shoulder and smiled at him. And he’d definitely felt it when Sonny had crushed him in a hug.

He liked feeling that small and vulnerable. The one that needed protecting, rather than the protector. It made him feel safe and warm in a way that he wasn’t really familiar with.

It made him fantasize about more than hugging, truth be told. The idea of being pinned down and taken, dominated by some strong man, made his stomach knot together in desire. 

He’d experimented a little in the shower, letting a soapy finger slide between his own ass cheeks and into his hole. It always burned a little, but he liked the forbidden feeling of it. Especially when he jammed it in deep and found that sweet spot that simultaneously made him want to pee and come, never sure which would come first. 

How would it be to let someone do that to him, he wondered. To just spread his legs and let some guy go to town on his ass, fuck him into the mattress. How would it be to let Sonny do that?

His Dad would fucking hate the idea, that was for sure, which only made it more interesting at that moment. 

Over the next week or so, Dean asked Sonny for countless hugs. The man always obliged happily, pulling him in with ease. Each one had the same safe feeling, and each one made him crave more. 

Dean finally took his chance one night when he knew that Sonny was the only adult in the house. 

He crept out of bed, careful not to wake any of the other boys. Even though it was pitch black in the main house, he found his way to Sonny’s room effortlessly, feet light and noiseless on the floor. A hunter’s step, his Dad would’ve called it. 

He lightly knocked on the bedroom door, certain that Sonny would still be up. Sure enough, he heard a soft answer from the other side and stepped into the room. 

“Dean? What are you doing out of bed?”

“I just wanted to talk to you…”

“Sure, buddy, we can talk.”

“Can I get a hug first?”

“God, I’ve created a monster, haven’t I,” Sonny said with a smile. But he was already sitting up in bed and opening his arms. 

Instead of answering the hug awkwardly from the side of the bed, Dean moved quickly to straddle Sonny’s legs. 

“Woah, kid, watcha doing?”

Dean had always learned that actions spoke louder than words, so instead of answering the very valid question, he leaned in and kissed Sonny soundly on the mouth. 

The older man made a surprised sound and gently pulled Dean away by the shoulders.

“Listen Dean, I think we need to talk.”

“I don’t really wanna talk, Sonny. I know I’m young and I haven’t done this kinda thing before. But I want this from you. I honestly do. You make me feel safe and warm and every time you look at me I just want to bend over…”

Getting the words out wasn’t easy, but he knew that he could trust Sonny not to laugh in his face.

The man wasn’t laughing, at least. Instead he scrubbed a hand over his face in a helpless gesture and looked Dean square in the eye. There was a heat there that Dean didn’t recognize, which only intensified the churning feeling of arousal and nerves in his gut. 

“Dean… This ain’t proper. You’re in my care. No matter what age you are, I’m responsible for you. I can’t let myself… Can’t expect you… I just –”

“It isn’t like that. My Dad is gonna pick me up in no time. He just left me here to punish me for my stupid mistake and when he’s done doing that, I’ll be back with him and Sammy. You’re not responsible for me. I’ve been taking care of myself and my brother for as long as I can remember. All I’m asking is for you to take care of me in this.”

He felt a little winded from that speech, but at least it shut Sonny up. Sonny, who was now looking at him with a frighteningly intense look in his eye that made Dean want to squirm.

The silence dragged on and Dean was almost ready to bail on the whole stupid plan, and then he felt a large hand cup the back of his head in a gentle gesture. 

Sonny smiled at him, a smile that made Dean feel warm all over, before pulling him in for another kiss.

It felt like victory and surrender all in one. Sonny plundered his mouth, mapping out every contour and battling with Dean’s own tongue. All while gentle stroking his hair, the side of his face, his neck. 

Dean had never felt so safe in his life.

His dick was quickly rising up and joining the party. The ratty pajama pants he was wearing didn’t do much to keep it in check and the fabric caught on his rapidly leaking head. 

It brushed against Sonny’s belly, who stopped the kiss for a moment to look down with a heated gaze. 

“You wanna be touched, Dean? Is that what you meant by taking care of you?”

“I wanna be taken. I wanna be fucked so hard the boys will notice my limp in the morning.”

“Damnit, boy. The things you do to me…” 

Sonny growled and crushed their mouths together again. Dean moaned into the space between their lips, thrusting his hips forward.

“God help me, but I’m gonna give you what you want.”

With those words, he wrapped one arm tightly around Dean and flipped them over. Dean landed on his back with a breathless feeling, looking up at the large man looming over him.

“Anytime you feel uncomfortable or wanna stop, you tell me, all right Dean? I’m not kidding around here. I don’t wanna hurt you.”

Dean nodded emphatically, not trusting his voice enough to speak right now. 

“Now let me see that gorgeous body of yours.”

He didn’t have to say that twice. Dean wasted no time chucking his shirt and pushing down his pants, leaving him completely naked. He felt Sonny’s gaze sliding over his body and had to resist the urge to cover up again. 

“God, you’re beautiful. Can I touch you?”

“Please…” 

Instead of reaching for his leaking dick, Sonny softly stroked Dean’s sides, his chest, all the way up to his nipples. The feather-light touches made him shiver.

Sonny pinched a nipple experimentally, grinning when Dean arched into it, moaning loudly. He bent over to flick it with his tongue instead.

Dean couldn’t believe how good it felt. He’d never really given any attention to his nipples and from the electric sensations he was feeling now, that had been a big mistake. 

His body was being worshipped, there was no other word for it. Dean felt himself sink into a haze as every inch of it was kissed or licked, tongue moving slowly downwards.

By the time Sonny had reached his dick, which lay throbbing against his stomach, Dean was craning his neck to look his partner in the eye and felt ready to start begging.

But Sonny just gave him a teasing smile and kissed the wet head once before sitting back on his haunches. 

Dean’s hips bucked up for a moment in frustration before they got pinned by strong hands.

“Show me what you want, Dean.”

Without hesitation, Dean lifted his legs and brought his knees to his chest, exposing his hole to the man in front of him.

The curse it brought out from the other man told him it wasn’t a bad view. He grinned mischievously.

“I did tell you what I wanted, didn’t I?”

“You sure did. And I’m gonna give it to you, D-dawg.”

With those words, he bent over again and started kissing his way down Dean’s leg. The skin on the back of his thighs was sensitive and the soft kisses made him shiver. Dean yelped when Sonny nipped the skin with his teeth, quickly soothing again with his tongue.

It took Dean some time before he realized exactly where Sonny was heading, and he nearly protested when he felt a warm breath ghost across his hole.

That was all the warning he got before a wet tongue began lapping at his furled opening. 

It was a strange sensation, but not a bad one. Once he got over the idea of it, he felt himself beginning to relax into it. Sonny seemed to notice, cause he backed off for a moment and stroked Dean’s quivering flanks.

“That’s right, boy. Give yourself over. Let me take care of you.”

Dean did exactly that, letting the sensations wash over him. His dick kept begging for attention, but he ignored it in favor of the amazing things that were being done to his ass. 

Sonny let a finger join and slid it in next to his tongue. It was broader than Dean’s finger had been, burning just a little as it slid in easily, slicked with spit. When it reached his sweet spot, Dean cried out.

Sonny chuckled and purposefully rubbed against it again, making Dean buck and moan. He started stretching out Dean properly then, getting help from a bottle of lube he apparently kept in his nightstand. 

Two large fingers were pumping in and out of his hole, stretching and burning as they went along. But the pain was nothing compared to what he was used. When a third finger was added, Dean made an effort to open his eyes and look at Sonny.

The man was palming his hard cock through his sleep pants as he fingered open Dean’s ass. It was an amazing sight and Dean felt like he could come without even being touched. But he wanted that cock inside of him first.

“Please…”

“You getting impatient on me now?”

“I want your dick in me…”

“Fine, because you’re asking so nicely. But I’m using a condom, that’s nonnegotiable.”

Sonny quickly shucked his pants, hard cock smacking to his stomach. He reached for the nightstand again and put on the condom in a practiced move. 

Dean felt sorry he couldn’t play with Sonny a little before, but he supposed there would be plenty of time for that after this and right now he was pretty desperate to get to the main event.

Sonny settled himself between Dean’s spread legs and lined himself up. Dean felt the blunt pressure against his hole, larger than he’d thought possible. But he forced himself to relax and accept the intrusion. 

It was slow going, a burning push inside, his insides trying to make room for the large dick. His erection flagged a little as his focus went to the discomfort.

When Sonny was fully seated, he held still and grabbed Dean’s dick instead. He flicked a thumb over the head and started jerking him off, effectively bringing Dean’s arousal back to full power. 

When Dean had accommodated to the unfamiliar feeling of being completely filled, he gave a little nod to Sonny. The man took that as the invitation it was and began slowly pulling out again, stopping when the head caught on Dean’s rim. Then he slammed back in with a force that knocked the breath out of Dean.

Sonny set a punishing pace, getting his hands on Dean’s ass and hoisting him higher. The change in position meant that nearly every stroke hit Dean’s sweet spot and brought him ever closer to his orgasm.

He felt the constant gaze of Sonny on him and looked at him. Despite the rough rhythm the man had set, his eyes were full of tenderness. They made Dean want to look away, or cry, but he didn’t break eye contact. 

That look, more than the cock currently fucking him hard, made him feel vulnerable and exposed like never before.

He just about got a hand on his dick before he came hard over his own chest and stomach. 

The sight of him coming must’ve set off Sonny as well, because the pace picked up and after a few punishing thrusts, Sonny buried himself deep, coming in long spurts. Dean could feel the dick inside him twitch, pumping the condom full, and shivered again.

He pulled Sonny towards him, letting the big man’s body cover his own. He felt as if he could disappear under that body, just lie there forever in the warmth and safety of this man.

He was asleep before he could feel Sonny pull out of him.


	2. Dean/Sam

**Summary for the Chapter:**

> With his trip to Hell coming closer, Dean could feel the desperate thing between Sam and him growing. After they face the trickster again at some stupid Mystery Spot, Sam finally cracks and makes the first move.
> 
> Set in season 3.

The first time Dean spread his legs for family, he was definitely old enough to know better. He should’ve seen it coming, though. Sam certainly had. 

It had always been there between them, this forbidden thing that Dean never dared to face directly. The last year it had been building even more strongly, brought to the surface by his impending trip downstairs. 

Sam had been so furious when he found out about the deal, so much that it had frightened Dean. But the further along his year got, the more Sam’s fury and determination slipped and Dean saw the desperation underneath. 

He’d tried to ignore it in true Winchester fashion, cause why talk about something you can’t change? It killed him to see his kid brother like that, though. He should be the one to take away that pain, not cause it. But nothing he could say would comfort Sam, he knew that much.

And then there was the other thing he sometimes saw in Sam’s eyes when they landed on him. Something heavy and lingering, that made Dean’s skin feel too small. He had even less of an idea what to do with that.

Okay, Dean wasn’t a complete idiot. He never claimed to have anywhere near the brain his little brother had, but he knew when something was staring him in the face.

He knew that normal brothers weren’t as close as Sam and he. He knew that this feeling of restlessness whenever Sammy’s focus wasn’t completely on him was weird. That selling his soul rather than living in a world without his brother wasn’t healthy.

But his default state, the thing that was engraved in every fiber of his being, was to keep Sammy safe. And on occasion, that meant from himself as well. So whenever his thoughts turned that way, he shoved them down into a little box marked do not open. Whenever he was fisting his dick and an image of hazel eyes and shaggy brown hair popped in his head, he got out a copy of Busty Asian Beauties and focused himself completely on that. And if that didn’t work, he’d go out to a bar and fuck some faceless, nameless guy until the urges went away.

It was wrong, that much was sure, to covet your brother. Dean only wished he knew how to stop it.

So when it finally did happen, Dean wasn’t too surprised. He knew that Sam would be the one to take the first step. He was the brave one, after all. That some kooky, fake mystery spot was the thing to finally crack Sam, did catch Dean off guard. He figured more had happened there than Sam was letting on, but still.

They had found a new motel, far away from that whacked place where he’d apparently died about a hundred times, and Dean was feeling good. He was with his brother, Baby had gotten some miles under her, they’d found a motel that was surprisingly not filthy and there were warm burgers waiting to be unpacked and eaten. Life was, within the parameters of their existence, pretty good.

As soon as the door closed, though, Sam had rounded on him and pushed him against the door. Dean didn’t even bother to fight back, too surprised with the sudden force of it. There was barely an inch of space between their bodies and he could feel Sam’s warm breath on his face.

“Dean… You gotta let me.”

“Wha-?”

“Let me touch you. I know you want it too, I see the way you look at me.”

There they were, the words that Dean had always dreaded. He closed his eyes in defeat. 

“Sammy… You gotta believe me, I never would’ve done anything. I never would’ve hurt you like that.”

“You can’t hurt me, Dean. I want you to touch me, too. I wanna feel you.”

“You don’t want that. You can’t want that.”

Sam backed off a little and Dean let out a breath he didn’t knew he’d been holding. There was a frown on his brother’s face that predicted trouble.

“What do you mean, I can’t want that?”

“I mean that… Jesus, I know I’m fucked up, but you don’t have to be. I’ll be gone in a few months and then you can finally get on with your life. Go for that law degree, the wife and 2.5 kids. I know that’s what you really want, what I dragged you away from.”

“God Dean, you can be such an idiot sometimes. That was never my first choice. It was always you. For as long as I can remember, it has been you. From when I was five and wanted to marry you. Or when I was twelve and jacked off for the first time to the image of you coming out of the shower. Or –”

“Stop! Sammy, don’t say that.”

“And why not? It’s the truth.”

“Cause that means I fucked you up even worse than I thought. I want something better for you, goddamnit!”

Sam’s face got hard, as it sometimes did when he heard Dean putting himself down like this. He backed up even more, sitting down on the bed, and Dean was just readying himself to slink away and pretend this hadn’t happened, when Sam spoke again.

“Come here, Dean.”

Sam’s voice was deep and raw and his tone made it clear that this was an order, not a request. When Dean didn’t react immediately, Sam growled and spread his legs.

“Come here and get on your knees right fucking now, before I drag you there.”

That voice did things to Dean. It made him want to submit, just as he had for Sonny all those years ago. He felt his feet carry him towards the place Sam directed without him consciously deciding to. Only when his knees hit the carpeted floor did he notice his little brother looming over him.

“Since you seem incapable of understanding what I want, I’ll just have to show it to you.”

With those words, he cupped the side of Dean’s face and surged in for a kiss. 

It was… a bit weird if he was being honest. Sam’s smell was so familiar to him, so entangled with his sense of home and belonging, but he wasn’t used to having it so close, to be actually tasting it. 

His brother didn’t seem to have the same hesitation though, judging from the way he ravaged Dean’s mouth, and Dean happily submitted to his little brother’s tongue. 

When Sam finally backed off, he felt a little light-headed and he was so hard in jeans it hurt. That situation wasn’t helped by Sam undoing his own jeans, revealing the equally hard boxer-covered bulge underneath. 

This time, he didn’t need any prompting from Sam, but just sort of fell face-first in that tempting hardness. He groaned as he mouthed the outline of his brother’s cock, already addicted to the smell.

“Take it out, Dean. I wanna see you suck it.”

“Who would’ve thought you were such a bossy bitch in bed,” Dean couldn’t help commenting. He was still a big brother, after all. 

“Shut up, jerk.”

Sam sounded a little breathless himself, and Dean wasted no time pulling down the boxers in front of him.

Sam’s dick was huge, bigger than his, Dean thought a little dismayed. It was gonna feel amazing in his mouth, he though immediately afterwards.

He licked the tip experimentally, tasting the dry skin and a drop of precome already welling. It tasted just like any other dick, but somehow better because it belonged to Sam. 

Dean couldn’t help the moan that escaped him and he quickly stuffed Sam’s cock in his mouth to muffle himself. It felt even better there, hot and heavy on his tongue. He let it slide a little further, to see how deep he could go before gagging. 

He quickly found that with some patience and careful concentrating, the answer was pretty damn far. And judging from the sounds Sam was making, it was greatly appreciated. 

Dean lost himself in the act, occasionally pulling off to mouth at the shaft and slightly furry balls, giving his increasingly tired jaw a little rest. Sam’s hand was buried in his hair, not pulling but simply holding and stroking. 

After a while, another hand came to cup Dean’s jaw and he was pulled upward again towards Sam’s lips. 

Their second kiss had none of the weirdness. Having your brother’s cock in your mouth can do that, Dean supposed. It also made him fully appreciate what an awesome kisser Sam was. He tried to give as good as he got, but it was clear who was in charge of their kiss. And he fucking loved surrendering. 

Sam bent forwards suddenly and, without breaking their kiss, got his huge hands on Dean’s ass and simply heaved him upwards, until Dean was thrown into his little brother’s lap.

This blatant display of strength drew a whimper from him, which only seemed to spur Sam on. The hands on his ass squeezed and grabbed, digging fingers between the cheeks and pressing, even through the rough material of his jeans, against his hole.

“I am going to fuck you tonight, Dean.”

“Oh god…”

“Sam will do.”

“I hate you.”

“Nah, you love me.”

“I love your dick. Very different.”

“Then you’re gonna love my dick inside your ass.”

“Why don’t you stop talking and get to it, then?”

Sam pulled back just a little, enough to look Dean in the eye.

“Have you ever had something in your ass?”

Dean rolled his eyes. Of course Sam would want to talk about it. 

“Yeah, I’m not some kind of blushing virgin.”

“I know you aren’t. So you’ve been fucked?”

“Just the once. I usually prefer to do the fucking.”

“When?”

“God, Sam, does it matter?”

“It does to me.”

“Let’s keep that story for another time, okay? Right now I’d much rather focus on this amazing dicking you keep promising me.”

“Fine, jerk. Then you’d better lose some clothes.”

Now that was a thing Dean could get behind. He enthusiastically stripped his shirts, getting his head stuck for a moment until Sam helped him out. Before he could contemplate removing his trousers while sitting on someone’s lap, Sam had lifted him up and thrown him on the bed in one smooth movement. 

Dean huffed a breath of air as he landed with a heavy thump on his back, but before he could recover Sam was already undoing his pants and stripping him fully. This manhandling was fast becoming a habit of Sam’s, it seemed. 

There was a moment of embarrassment, as he looked down his own naked body and up to Sam’s larger one, looming above him, still in his shirt and opened pants. Dean had to suppress the urge to cover himself up and he felt a blush creep up his cheeks. 

Sam just looked… hungry. There was no other word for it. The strangeness of this whole thing struck Dean again. Not one of the many secret fantasies he’d amassed over the years could compare to the realness of this, the smell of Sam’s sweat and the feel of his calloused hands. It was desperately familiar and wholly alien at the same time. 

Sam stripped quickly and efficiently and got something from his duffle, before crawling between Dean’s slightly parted legs. 

He kissed Dean again, deeply and briefly. Then he pressed a kiss to Dean’s jaw and moved lower to his neck. It seemed Sam was intent upon worshipping every inch of his body, moving methodically from his neck to his chest and abdomen. His nipples were licked, which sent unexpected electric thrills through him, but Sam was already moving downwards. 

Dean’s dick was standing proud, leaking at the tip, practically begging to be touched. Sam, asshole that he was, kept avoiding it, though. Instead he lightly nipped at Dean’s hipbones, inner thighs, even licked his balls, everything except the drooling cock. 

Sam ran his hands up Dean’s legs, spreading them wider and finally upward, bringing Dean’s knees towards his face and effectively putting him on display.

“Hold these for me, would you?”

Sam casual tone as he asked Dean to hold his own legs up had Dean’s cheeks burning bright red, but he did as told. Nothing about this situation made him doubt who was really in charge.

When his brother continued his exploration with tongue and teeth, Dean realized where this was heading. The first touch of Sam’s tongue to his asshole still made him jump.

“Hold still,” Sam admonished, and slapped his ass lightly.

With those words, he dove in and started rimming Dean in earnest. 

It felt fucking amazing.

Some women had gone there in the past, tentatively trying it out with the very tips of their tongues. And of course Sonny had been the first one to introduce him to the practice. None of them could compare to this ravenous tonguing, though. Same ate him out like a starving man at a buffet, and made the sounds to match.

It made Dean a little light-headed and drove away all thoughts of shame or embarrassment. This alone was completely worth going to hell for…

By the time Sam pulled off, Dean was panting and whimpering, arms shaking with the effort of keeping his legs as far back as he could.

His little brother grinned at him, mouth shiny with spit. Evidently, he liked reducing Dean to a whimpering mess. Little fucker.

Sam clicked open the bottle of lube he had put on the bed and squirted a generous amount on his fingers. The first touch of the cold lube to his ass made Dean tense a little, but Sam’s hard work had succeeded in making him so pliant that the first finger practically slid in of itself.

Dean groaned long and loud at the feeling of finally having something fill him up. Sam’s finger was thick and perfect, making room for itself. It was quickly joined by a second finger, which only burned a little, and then Sam began fingering him properly. 

The look in Sam’s eyes was dark and promising and it made Dean shiver. Neither of them seemed able to break eye contact as Sam continued to stretch out his ass. 

Dean lost himself in the gaze of his little brother, finding there a mirror image of the depth of feeling he was so bad at articulating. 

He knew Sam would always be there for him, just as he would for Sam. It was of course what had gotten them in trouble so many times before, but that seemed trivial now. 

He was shit at saying any of this, but Dean could feel the connection between them as if it was a living thing. It was beautiful. Sam was beautiful. And Dean desperately wanted him inside.

“Come on Sam, I’m ready.”

“Are you sure?”

“Yeah, come on. I’ve waited long enough.”

“You’re telling me. We could’ve been doing this for years if you hadn’t been so stubborn.”

“Shut up and get over here, bitch.”

Sam grinned at him and did as he was asked. He lubed himself up and inched closer, until that monster dick of his was nudging at Dean’s entrance. For a moment, it seemed impossible as the pressure against his asshole increased to painful levels, and then the stretched muscle gave way and the head of Sam’s dick slid inside.

It made both of them gasp, still looking at each other in mutual amazement. Sam took over the hold on Dean’s legs as he slid in to the hilt, blanketing Dean’s body with his own.

He couldn’t remember his time with Sonny feeling quite this… overwhelming. Or maybe it just had been too long since he’d been properly filled like this.

Either way, the drag of Sam’s dick inside his ass felt amazing, painful burn quickly fading. Sam started rocking carefully, testing out the waters. When he nudged Dean’s sweet spot on the second try, Dean saw sparks and let out a loud cry. 

“There it is,” Sam grinned.

With that, he began fucking Dean properly. His little brother had some power behind his thrusts, and made Dean practically incoherent. 

He lost himself in the sensations, feeling his orgasm build to the point where any touch might have set him off. But his dick was still conspicuously ignored. When he tried to reach it himself, his hand was pushed away.

“Please, Sam…”

“Please what?”

“Please touch my dick, I wanna come.”

“You can come on my cock, or not at all.”

“You gotta be kidding me!”

“Nope, dead serious.”

“Sam come on, I’m so close. Just let me touch it if you don’t wanna.”

Sam grinned again and shook his head, capturing Dean’s mouth with his instead. 

All the kisses in the world couldn’t make Dean forget how desperate he was to come, though. He’d never come untouched and was pretty sure he couldn’t, but his brother seemed pretty set in his decision.

The thrusts became even harder, hitting his prostate nearly every time now. Impossibly, Dean felt himself get closer and closer. Then Sam brought his mouth to Dean’s ear.

“Come for me, big brother.”

With those words, he bit hard in the crook of Dean’s neck and Dean could feel himself fall over the edge, shouting his brother’s name.

Finally, a big hand close around his dick and helped him milk out the remains of his mind-melting orgasm. Dean was still trying to wrap his head around what had just happened when Sam’s thrust became erratic and he felt his brother shoot his load deep in his ass.

Sam collapsed on top of him, breathing heavily. Dean would never say it out loud, but he liked the feeling of having this heavy, sweaty body covering every inch of him. 

They lay there in silence for a while and Dean felt his brain slowly coming back online. 

There was a softening dick in his ass, which was throbbing a little by now. His neck ached from his lunatic little brother’s teeth and his leg muscles were sore from the position they had held. 

All in all, he felt pretty awesome. Still, he couldn’t resist nagging just a little. 

“You bit me, freaking vampire.”

“And you came untouched. You’re welcome.”

“Bitch.”

“Jerk.”

Dean smiled in Sam’s hair. Some things would never change, no matter what happened between them. 


	3. Dean/Benny

**Summary for the Chapter:**

> Dean is trapped in Purgatory, with no one to rely on except this vampire. As they continue their search for Cas, they get closer.
> 
> Set in season 8.

**Notes for the Chapter:**

> I suck at summaries, but here you go. Basically just Dean/Benny smut, as advertized. 
> 
> Hope you enjoy!

The first time Dean spread his legs for a monster, he was afraid he was becoming one himself. 

Purgatory was slowly eating away at the edges of his humanity. He could feel it, day by day, letting the beast inside himself take over.

He knew Benny was the only thing that kept him sane in this stinking mess of run, fight, kill, repeat. The one person he could talk to, the only one who had his back.

It made him laugh sometimes, this thought that a vampire was the thing keeping him human. If only his Dad could see him now. Or Sammy…

Thinking of his brother hurt. He imagined Sam doing all kinds of horrible shit right now, trying to bring Dean back. 

“Dean!”

His head jerked up at the sound of his name, only to find himself surrounded, some filthy thing already putting their hands on Benny. 

Dean shook off the pointless worry about his brother to focus on the danger a little closer to home and sprang to his feet, already assuming a fight stance. 

The serrated knife in his hand felt at home there, like an extension of his arm. This was how it had always been, right? 

He quickly took stock of the situation. A nest of vamps from the looks of it. Two bloodsuckers at his back, another two trying to subdue Benny and clearly failing, and one advancing on Dean. 

Dean shot forward towards his assailant, putting space between him and the two at his back. Before the thing knew what was happening, Dean had already sliced through its neck and watched the head thump on the ground. 

“You need a hand, Benny?” he asked without taking his eyes off the body in front of him. 

“Nah, brother. I got this.”

The familiar Southern drawl made Dean grin, and he spun around to find the other two vamps coming at him, fight faces on.

“Come and get it, bastards.”

His blood sang as he spun and sliced, in a sort of fucked up dance. This was where he felt truly at ease. This was what he was good at. 

The blood suckers never really stood a chance. He took them out efficiently, getting a few scratches out of the deal but nothing major. 

When he turned to help out Benny, it was to already find the last two vamps dead on the ground, a panting Benny standing over them.

Dean laughed at that, pulling his brother in arms in a one armed hug.

“Thanks for the warning, dude.”

“Maybe if you didn’t have your head in the clouds, Cher, you would’ve heard them coming.”

“Yeah, yeah.”

“Now, let’s keep this party moving, shall we?”

Dean nodded and they took off again, walking at an easy pace. He enjoyed the remainder of adrenaline coursing through his body, chasing away the aches and discomforts, leaving him pleasantly buzzed. 

It was Benny who eventually broke the silence.

“So, what’s keeping that pretty head occupied?”

“Nothing, man. Just hoping my little brother isn’t doing too much damage getting me outta here.”

“He’s human, ain’t he? How much damage can he do?”

Dean chuckled at that. 

“Dude, you don’t wanna know. Sam and me, we’ve managed to fuck things up pretty well for two humans.”

“That sounds like a story worth telling.”

“More like a hundred stories, but sure.”

“Well Cher, we got nothin’ but time in this godforsaken place. How about you entertain me?”

Dean glanced at his friend, amused. Benny just smiled back, confident and cool. That smile never failed to make Dean’s insides squirm with a dark, hot feeling that he wasn’t too keen on examining at the moment. 

Instead, he cleared his throat and thought of a good place to start.

“When Sammy died the first time, I sold my soul to bring him back-”

“Hold on a sec there, darlin’. The first time?”

“Sure, me and Sam may still be human, but we’ve been around the mortality block a few times.”

“Well, this sure is gonna be interestin’. Continue.”

“So, a year after that, the Hellhounds came and dragged my ass to Hell. I held on through some thirty-odd years on the rack before I cracked and started putting souls on myself. Turned out that decision kickstarted the apocalypse. I spent another ten years learning the art of torture before Cas rescued me.”

“Cas, as in the angel we’re risking our lives for currently?”

“The very same. It’s how we met, actually. I used to have this big ass handprint of his on my arm from where he pulled me out.”

Benny whistled through his teeth.

“Damn. So how old are you then, really?”

“Huh, never really thought about it. My body’s 33, but I guess my mind’s more like 73. Huh.”

“You look good for your age.”

“Right back at ya. So, when I got back, it turned out that Sammy had been working with a demon to try and get me back. What I didn’t find out till much later was that he’d gotten himself addicted on demon blood and was manipulated into setting Lucifer free, actually starting the apocalypse.”

“I sure missed some things stuck here.”

“Not sure that many people noticed. We managed to cram the Devil back in his cage, only Sammy had to jump in himself to make it work.”

“So your brother is stuck in a cage in Hell with Lucifer?”

“No, that didn’t stick. First his body was brought back by Cas, so he walked around as a soulless psychopath for a while before I found out and convinced Death to get his soul outta the cage.”

“Death? You mean a reaper?”

“Nah, they wouldn’t have the juice. I mean actual Death, the big man himself. He likes junk food.”

“Sure… Continue.”

“So Sammy got back, but with a wall in his brain to make sure that a hundred years of torture in Hell didn’t break through. Then it turned out Cas had gone dark side to win some civil war in Heaven and was trying to get at the souls in Purgatory. When we tried to get in the way, he broke Sam’s wall and nearly killed him.”

“Now there’s something I recognize. We were stuck in that angel for a while, weren’t we?”

“I guess you were. How was that?”

“Crowded. I don’t remember much of it to be honest. Though it seems more empty here, now.”

“Lucky us.”

“So, hang on. If your angel went dark side, how come we’re now risking our lives trying to find him?”

Dean sighed deeply. The million dollar question.

“Because… he’s Cas, man. He risked his life for Sam and me more times than I could count. Yeah, what he did was fucked up, but he did it because he thought he was doing the right thing. Which is usually how Sam and I also end up in trouble. So, you know, I can relate.”

“I get it. Some people you can’t let go, no matter what they do.”

“Yeah? You got someone like that?”

“Oh sure, I left my girl behind when I died. I would’ve done anything to save her, too. Couldn’t, though.”

There was bitterness in his voice, built up by years of grief. Dean glanced at his friend while they were walking. Benny seemed lost in his thoughts for a moment.

“I’m sorry, dude. Love sucks.”

Benny seemed to shake himself out of his reverie and looked back at Dean, sly smile on his face.

“So tell me, then. What’s the deal with you and this angel?”

“What deal? He’s my friend.”

“Cher, that’s not gonna fly with me. I see the way you talk about him.”

“And what way is that? Cause it’s just a friend way, I tell you. Besides, I like girls.”

“I bet you do. But are you tryin’ to tell me you only like girls? Cause that I don’t believe for a second.”

The words shocked Dean and he suddenly felt inexplicably exposed. This was a side of himself he’d always tried to hide and he thought he was pretty good at it. For someone to just see it… Fuck. 

Benny seemed to notice Dean’s discomfort, cause he clapped a hand on his shoulder and spoke again.

“It’s okay, Cher. I’m not gonna out you. We just tend to recognize our own, is all.”

The implications of this slowly sank in and Dean looked Benny with surprise on his face. 

“Really? Even with that girl of yours?”

“Doesn’t mean I’m suddenly blind. I can still feel attraction. Never much cared what gender that came with, either.”

“Huh, wouldn’t have guessed it.”

“So you like cock, too?”

Dean blushed at the forward question. He’d never talked to anybody about this. Still scared of the prejudices that might come his way if he did. 

“Um, yeah, I guess…”

“Does this make you uncomfortable, Cher?”

“Just not used to talking about it, that’s all. No big deal.”

“I agree. It doesn’t have to be a big deal. Sometimes it can just be a bit of comfort.”

Dean dared a glance towards Benny and saw a crooked smile there that predicted trouble.

“You offerin’ some comfort?”

“Might be. Pretty boy like you, can’t say thought hasn’t crossed my mind.”

Dean decided to act on instinct. In a split second, he’d rounded on Benny, tackled the man to the ground and straddled him, knife to the neck.

“Yeah? You just like me for my pretty face?”

The words were harsh, but he couldn’t keep the playfulness out of his voice. It felt almost like roughhousing with Sam when they were little. All bark and no bite.

Benny smirked at him, seemingly unfazed by the sharp blade pressing down on his throat.

“Not just your face, darlin’.”

Before Dean could respond to that, the world swirled around him and he suddenly found himself on his back on the ground, Benny’s large body looming over him.

His knife was knocked out of his hands and he didn’t even scramble for it. Benny invaded every one of his senses and he felt breathless with it. His legs opened of their own accord, making room for the bulky man.

“Atta boy. Now let me show you how pretty you are.”

The words seeped into Dean’s brain like warm water, and he shivered. 

There were filthy, the both of them. But the arousal sparked by Benny’s rough hands roaming his body overtook any hygienic concerns. 

If anything was gonna kill him in here, it sure wouldn’t be some stupid infection. 

Both of them recognized the need of efficiency in this hostile environment, and Benny didn’t waste any time undoing Dean’s jeans and yanking everything down. 

Dean’s dick lay throbbing against his stomach, already leaking at the tip.

“That is one pretty dick you have there, Cher. Gonna get my mouth on it.”

Benny proceeded to do just that, taking the whole thing down his throat. Dean nearly cried with how good it felt. 

Too soon, the vampire pulled off again. Dean uttered a sound of protest, which was quickly drowned out as he saw Benny suck on his own fingers, before pressing Dean’s legs even further apart and finding his opening.

The finger-fucking felt amazing, even if it was a little dry. Benny was clearly a man that knew what he was doing, and Dean’s rational mind was quickly checking out. He hoped one of them would notice if something came too close, but at this point he found it hard to care about that.

“You ready for me, Cher?”

“Yeah, Benny, come on. I need you.”

“Don’t worry, I’m gonna give you what you need.”

With that, he pulled out his own, rather intimidating hard-on, slicked it up, and wrapped Dean’s legs around his waist to get in a good position.

When Benny breached him, the stretch of it was nearly too much. It burned, and he hadn’t had enough prep. But somehow, the violence of it all fit perfectly with this place. 

It was what he wanted. He wanted to feel the pain of it, the overwhelming stretch and following fullness. This, just like the battles they fought every day, made him feel alive. 

It made his blood sing and his heart race. It made him look up into Benny’s eyes and get lost in there.

“It’s okay, I got you. Let go.”

Strangely, Dean believed him. In that moment, he trusted the man above him completely. And he did let go.

He clung unto Benny’s back with all his strength, feeling every punishing thrust rub that spot inside him. His erection was trapped between their bodies and he buried his face in Benny’s neck.

He heard a strange keening noise and realized it came from him. His face felt wet and he had the sneaking suspicion that he was actually crying. 

But it didn’t matter. All that mattered was the feeling of Benny all around him, consuming him as he got fucked with supernatural strength.

It was the most overwhelming experience he ever had.

He did come at one point, spurting jizz between their stomachs, but it barely even registered. He felt completely and utterly owned.

When Benny came, he could feel his cock twitch inside and the other man’s thrusts finally slowed down.

They stayed like that for a long time, both breathing heavily, both unwilling to let go of each other just yet.

Soon, they’d have to disentangle themselves, get dressed again. They’d go looking for Cas again, try to find a way home. 

Dean wondered if he would even recognize himself if he ever got there.

His eyes snapped open at a sudden noise, and he was startled to see a figure standing there.

It was Cas.

Cas, standing there with wide eyes, looking at the both of them. There was no mistaking what had happened here. Hell, Benny’s dick was still inside of Dean.

They stared at each other, both of them lost for words. And then Cas blinked out of existence.

**Notes for the Chapter:**

> Kudos and comments are always appreciated :)


End file.
